What happens when founders build something meaningful, sell it, and realize the next chapter is not as clear as expected?
In this episode of The Pleasant Street Pod, host Taylor Nissi, CFP®, CEPA, sits down with serial entrepreneur and private equity investor Chris Cali to unpack the real journey behind building, scaling, and exiting a business, and what most founders do not anticipate along the way.
Chris discusses:
- The early “ramen and rent” phase of entrepreneurship and how personal finances often take a back seat
- The reinvestment dilemma founders face as businesses begin generating real cash flow
- Lessons learned from selling two companies, including why the highest offer is not always the right one
- The emotional and identity shift many founders experience after an exit, and why planning the next chapter matters
And more!
Resources:
- Strategic Wealth Scorecard (2-minute assessment): Strategic Wealth Score Card
Connect with Taylor Nissi:
- Pleasant Street Wealth Advisors
- LinkedIn: Taylor Nissi CFP®, CEPA
- Book some time with Taylor (Book 20 Minute Strategy Call)
Connect with Chris Cali:
About our Guest:
Chris Cali is a serial entrepreneur and private equity investor who has built and sold two companies in the technology services space. After starting his career as a software engineer, Chris went on to co-found and scale Spark Digital to hundreds of employees across the U.S. and Argentina before selling the firm to a private equity-backed strategic buyer. Today, he is a partner at Newfound Equity, where he works hands-on with founders to help grow businesses while preserving culture and long-term value.
About Taylor Nissi:
Taylor A. Nissi, CFP® CEPA, is a founder of Pleasant Street Wealth Advisors. As a Certified Financial Planner, Taylor provides high-impact financial advice and guidance to individuals, businesses, and families. Taylor also holds the Certified Exit Planning Advisor designation. As a Certified Exit Planning Advisor, Taylor works with business owners of all stages to help them build valuable transferrable businesses.
The Pleasant Street Wealth Advisors team is on a mission to help more people have confidence, peace of mind, and clarity in their financial life. When our clients reach that level of confidence and peace of mind in their financial life, they can spend more time and energy on the people and passions that bring them joy. We call that “Experiencing Your Wealth’s Possibilities.”
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Entrepreneurs and business owners.
Serves a national or global client base.
Based in Westchester County NY
High Net Worth individuals